3,5-Bis(trifluoromethyl)phenylhydrazine → 2-[3,5-Bis(trifluoromethyl)phenyl]-4,5-dichloropyridazin-3(2H)-one

HRID 1902831Notes

Reaction equation

HRID 1902831 reaction equation
[C:1](O)(=O)/[C:2](=[C:4](\[CH:6]=[O:7])/[Cl:5])/[Cl:3].[F:10][C:11]([F:25])([F:24])[C:12]1[CH:13]=[C:14]([NH:22][NH2:23])[CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=1>C(O)C>[Cl:3][C:2]1[CH:1]=[N:23][N:22]([C:14]2[CH:15]=[C:16]([C:18]([F:20])([F:21])[F:19])[CH:17]=[C:12]([C:11]([F:10])([F:24])[F:25])[CH:13]=2)[C:6](=[O:7])[C:4]=1[Cl:5]

Participants

4

Reactant 2

HCID 5229013,5-Bis(trifluoromethyl)phenylhydrazineHCID 2771871Mucochloric Acid

Product 1

HCID 205138102-[3,5-Bis(trifluoromethyl)phenyl]-4,5-dichloropyridazin-3(2H)-oneYield 90.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 28.1 grams (0.166 mol.) of mucochloric acid dissolved in 120 milliliters of ethanol were added 37 grams (0.151 mol.) of 3,5-bis-(trifluoromethyl)phenylhydrazine. The mixture was stirred for about one hour, and then the ethanol was removed from the solution by evaporation under reduced pressure. Eighty milliliters of glacial acetic acid and 80 milliliters of acetic anhydride were added to the residue in one portion. The mixture was heated to reflux for four hours, and then cooled and the solvent was removed by evaporation under reduced pressure. Recrystallization of the residue from ethanol produced 51.7 grams of 4,5-dichloro-1-[3,5-bis(trifluoromethyl)-phenyl]-1,6-dihydro-6-oxopyridazine.

Workup

  1. customthe ethanol was removed from the solution by evaporation under reduced pressure
  2. additionEighty milliliters of glacial acetic acid and 80 milliliters of acetic anhydride were added to the residue in one portion
  3. temperatureThe mixture was heated
  4. temperatureto reflux for four hours
  5. temperaturecooled
  6. customthe solvent was removed by evaporation under reduced pressure
  7. customRecrystallization of the residue from ethanol

Sources & evidence

ORD record
ord-7314461433054cebba4dd13451ba70f1
Source dataset
uspto-grants-1982_12
Patent number
US04366155

Reaction notes

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